Angewandte Chemie,
Journal Year:
2024,
Volume and Issue:
unknown
Published: June 3, 2024
Abstract
A
dearomative
oxidation
of
pyrroles
to
Δ
3
‐pyrrol‐2‐ones
is
described,
which
employs
a
sulfoxide
as
oxidant,
in
conjunction
with
carboxylic
acid
anhydride
and
Brønsted
additive.
3‐substituted
undergo
regioselective
give
the
product
isomer
oxygen
has
been
introduced
at
more
hindered
position.
Regioselectivity
rationalized
by
proposed
mechanism
that
proceeds
initial
thianthrenium
introduction
less‐hindered
pyrrole
α‐position,
followed
distal
attack
an
nucleophile
subsequent
elimination
thianthrene.
The
same
reaction
conditions
are
also
able
effect
chemoselective
indoles
indolin‐3‐ones
additionally
2‐hydroxyindolin‐3‐ones.
Here
again,
regio‐
chemoselectivities
through
intermediacy
salt.
Journal of the American Chemical Society,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 21, 2025
Thianthrenation
is
a
useful
strategy
for
the
late-stage
diversification
of
complex
small
molecules
owing
to
positional
selectivity
and
synthetic
versatility
thianthrenium
salts
as
electrophilic
linchpins.
However,
substrate-dependent
identification
suitable
reaction
conditions
thianthrenation
can
be
difficult.
Reported
functionalization
vary
significantly
and,
in
some
instances,
lack
robustness
practicality.
Herein,
we
report
generalized
approach
preparation
two
manifolds
practical,
robust,
parallel
salts.
European Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
26(43)
Published: Sept. 13, 2023
Abstract
The
utilization
of
aryl
radicals
as
open‐shelled
intermediates
has
become
an
essential
tool
for
both
conventional
and
state‐of‐the‐art
synthetic
chemistry.
However,
the
current
methods
generating
are
still
inefficient,
greatly
impeding
their
practical
applications.
Encouragingly,
sulfonium
salts
have
emerged
appealing
sources
a
wide
range
transformations
aimed
at
creating
novel
chemical
bonds
driven
by
distinctive
structural
attributes
tendencies.
This
review
primarily
focuses
on
specific
reaction
mechanisms
underlying
cleavage
C−S
in
salts,
leading
to
generation
corresponding
within
diverse
conditions.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(18), P. 3977 - 3981
Published: April 29, 2024
A
denitrative
cyanation
of
nitroarenes
using
organocyanides
and
a
palladium
catalyst
was
developed.
The
key
for
this
reaction
the
utilization
an
aminoacetonitrile
as
cyano
source
to
avoid
generation
stoichiometric
metal-
halogen-containing
chemical
waste.
wide
range
nitroarenes,
including
heteroarenes
pharmaceutical
molecules,
can
be
converted
into
aryl
nitriles.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(20), P. 5731 - 5740
Published: Jan. 1, 2024
A
simple
and
practical
method
for
the
synthesis
of
S
-alkyl
phosphorothioates/phosphorodithioates
through
three-component
reaction
cyclic
sulfonium
salts
with
8
,
H
-phosphonates,
or
P
4
10
alcohols
was
readily
developed.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(12), P. 2473 - 2477
Published: March 18, 2024
Here,
we
report
an
efficient
Pd(II)-catalyzed
Heck
coupling
reaction
utilizing
modular
and
readily
available
thianthrenium
salts.
The
tunability
ease
of
salts
facilitated
the
integration
glycals
with
drugs,
natural
products,
peptides.
This
method
allows
incorporation
diverse
into
structurally
varied
aglycon
components
without
directing
groups
or
prefunctionalization
provides
a
practical
for
synthesizing
C-aryl
glycosides,
offering
new
avenue
production
complex
glycosides
potential
applications.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(17), P. 12668 - 12680
Published: Aug. 9, 2024
Incorporating
a
sulfonyl
group
into
parent
molecules
has
been
shown
to
effectively
improve
their
synthetic
applications
and
bioactivities.
In
this
study,
we
present
straightforward
practical
approach
for
the
ring-opening
reaction
of
alkenyl–aryl
sulfonium
salts
with
sodium
sulfinates
produce
range
sulfur-containing
alkyl
sulfones.
This
method
offers
benefits
mild
conditions,
easily
accessible
raw
materials,
wide
substrate
applicability,
good
functional
compatibility,
operational
simplicity.
Importantly,
resulting
products
can
be
readily
converted
sulfoxides,
sulfones,
sulfoximines,
some
heterocyclic
compounds.
ACS Sustainable Chemistry & Engineering,
Journal Year:
2024,
Volume and Issue:
12(34), P. 12808 - 12818
Published: Aug. 15, 2024
Herein,
a
mechanochemically
triggered
C–H
arylation
of
coumarins,
quinoline-N-oxides,
and
uracil
molecules
with
aryl
thianthrenium
salts
is
described.
Aryl
are
primarily
acknowledged
for
their
expedient
reusability
adherence
to
atom
economy
principles.
Mechanistic
studies
suggested
that
mechanical
stress
promoted
the
homolytic
scission
C–S
bond
salts,
forming
radical
intermediate.
Later,
intermediate
engaged
in
addition
reaction
above
heterocycles,
leading
desired
products
good
yields.
This
versatile
protocol
accommodates
wide
range
functional
groups
facilitates
synthesis
bioactive
compounds
drug
molecules.
Abstract
Amines
are
widely
found
in
natural
products,
drugs
and
pesticides.
We
have
proposed
a
base‐promoted
method
for
synthesizing
polysubstituted
aromatic
amines.
The
reaction
does
not
necessitate
the
involvement
of
transition
metals,
provided
that
an
equivalent
base
is
employed.
In
this
process,
aryl
thianthrenium
salt
serves
as
precursor
to
arynes,
which
subsequently
distorted
by
induction
effect
different
substituents.
attack
amine
nucleophiles
results
formation
series
multi‐substituted
products.
